Armed with her single “You Oughta Know,” Alanis Morissette had a goal in mind: to remind an ex-lover of the mess he left when he went away. With 14.7 million copies sold of Jagged Little Pill, her U.S. debut released 17 years ago today, 21-year-old Morissette made her point loud and clear.

Sixteen years later, another 21-year-old foreign singer with a funky A-name made the same point – just in a different tone of voice.

In November 1995, Morissette was pictured on the cover of Rolling Stone next to a prominent cover line: “Angry White Female.” In April 2011, Adele appeared on the cover. Her cover line: “Heartbreak Superstar.” Does Alanis not chronicle heartbreak on Jagged Little Pill? Does Adele not come off as angry when she sings lines like “you’re gonna wish you never had met me” (from “Rolling in the Deep”)?

Adele’s 21 focuses on emotions that follow a breakup, from the vengeful “Rumor Has It” to the reunion plea of “Don’t You Remember.” With songs like “Head Over Feet” and “You Learn,” Jagged Little Pill could be considered more of a soul-searching examination of a failed relationship, from inception to fiery demise. The hardest breakups run the emotional gamut: “You Oughta Know” remains the go-to singalong for the pissed-off phase, while Adele’s “Someone Like You” is for what comes after. The wild success of both albums, according to Morissette, “speaks to the tender-heartedness of people.”

Morissette characterizes herself, Adele and other “artists who are so vulnerable yet in the public eye”: “We’re philosophers, we’re an archetype – inward-looking and sensitive to say the least.”

Their public personas, however, couldn’t be more different. When she debuted, Alanis was rock’s scorned feminist not to be fucked with, her magnum opus not exactly winning her sympathy (not that she was looking for it). Adele, a big-voiced blue-eyed-soul queen, had the world demanding to know who broke her heart simply so a proverbial ass-kicking (or at least some tersely-worded tweets) could be delivered to the fool. Yet in their respective moments, Alanis and Adele were both at odds with what was happening in pop music, filling a similar void via bitter breakup albums that doubled as coming-of-age tales.

According to Steve Barnett, the chairman and COO of Adele’s U.S. label, Columbia, “Rolling in the Deep” wasn’t shopped to pop radio until a week after 21 debuted at No. 1 in March 2011. The singlebegan with a push at AAA (adult album alternative) radio in November 2010, never intended to seriously compete with Top 40’s dance divas. Adele would eventually surpass the competition with nary a dance move, unless you count her expressive finger wagging.

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Likewise, “You Oughta Know” wasn’t expected to make it to radio, but eventually crept up through rock and alternative stations before finding a home on pop radio. During an era when TLC, Mariah Carey and Boyz II Men ruled the airwaves, Morissette scored five Top 10 singles on the Pop Songs/Top 40 chart. Alternative rock was having its moment, and Alanis was its crossover queen.

“Jewel, Meredith Brooks, Joan Osborne, Lilith Fair acts came out of the woodwork and got on the radio thanks to Alanis,” says Keith Caulfield, Billboard’s Associate Director of Charts/Retail. “It was all about female empowerment, and Alanis was getting her message to so many people who didn’t normally hear that kind of thing.”

The exposure, which Morissette likens to “riding the crest of a really big wave,” wasn’t exactly what she had hoped for, though. “Grabbing the brass ring of fame during that time was disillusioning and gorgeous in a way because it furthered my journey of inward-looking, since there was nowhere else to go,” she says. “The fame didn’t give me what it promised. It had promised to make everything OK, and it didn’t.”

Adele’s own story has little to do with celebrity. The singer distanced herself from pop stardom by declaring to Rolling Stone last year, “I don’t make music for eyes, I make music for ears” after mentioning the T&A of Katy Perry and Lady Gaga. But with “Someone Like You” topping the Hot 100 chart for five weeks, curiosity regarding Adele’s personal life peaked, much as it had with Alanis following the ubiquity of “You Oughta Know.” Still, Columbia’s Barnett views the single as “the critical point of audiences connecting with 21.”

In her primetime NBC special on June 3rd, Adele said that the tabloid “investigations” of the lover who inspired 21 has made her “wish she’d kept a lot of things to herself.” Morissette can relate: “When I wrote Jagged Little Pill, I just thought, ‘Hey now, maybe 100,000 people might hear this,’ which wasn’t that scary. Every album since then, I’m gripped with terror about what I wrote and who I wrote about the day before the record’s released.”

However, Adele and Alanis have been rewarded for their confessions. Had it not been for Taylor Swift’s Fearless in 2010, Adele would have broken Morissette’s record of being the youngest person to win the coveted Grammy award for Album of the Year. Neither are the first to write deeply personal albums and be awarded with sales nearing 10 million and Grammy accolades, but it’s an exclusive club whose only other member may be Fleetwood Mac’s Rumours.

“On 21 and Jagged Little Pill, the songs are about these very specific situations, but they hit you,” Caulfield says. “It’s a fine line, but that’s why these albums have been so successful – they manage to find a middle ground. They’re relatable to the masses, but at the same time, listeners get a small glimpse into another person’s heartache.”